My Jerk of a Crush
by Wolfsnivy700
Summary: Dawn is a teenager who moves to Veilstone City and begins to attend a boarding school. She meets several people there who are interesting, but will she gain an unexpected crush on an unexpected guy? This story will include mainly Ikarishipping and Advanceshipping, but it will also have Orangeshipping, and slight Flavescentshipping, and that's about it.
1. Chapter 1: New School

**Hi! This is my first story. It will contain Ikarishipping and a few others. I own nothing except the weird last names I made up for them! Enjoy!**

Dawn didn't want to move. She didn't want to leave her old friends, and most of all, she did not want to go to a new school, no way, no how. But that's what she got.

"Dawn, you're being dramatic," her mother had just said, simply. "It's just school."

"BOARDING school," Dawn corrected. "As in: I won't see you for over half the year school! I don't think I'm ready for this."

Dawn was a dark blue haired young teen, who had moved a couple days ago from Twinleaf Town to stupid Veilstone City. She only had one Pokemon, a tiny Piplup, that wasn't very strong.

"Don't worry, you'll make lots of friends!" her mother countered. "And, by next summer, I expect you to have a boyfriend," she teased.

"MOM!" Dawn said, blushing. "You're not going to need to worry about my nonexistent love-life."

That night, Dawn packed her stuff for school. She took her one Pokeball, containing Piplup, and put it in her backpack. Her mother suddenly entered with a small package.

"This is your new school uniform!" she said. Dawn tried it on. It had a navy blue skirt with black leggings underneath, and a white blouse.

"I feel like a character from Sailor Moon," Dawn commented, looking at her clothes. "But hey, not too shabby, for a school uniform."

That night, Dawn had weird dreams about what the school would be like, which were all pretty surreal.

The next morning, she got up early to put her hair up in the requested ponytail (also for the uniform), and ate breakfast. She hopped in her mom's car thirty minutes later with a sick feeling in her stomach.

When they pulled up at the school, Dawn felt her jaw drop. It was huge. She had no clue how she was going to navigate that building.

"Well," her mother said, turning to Dawn. "I guess you should get going." She hugged her tightly. "Make lots of new friends, okay?"

"I will," Dawn promised.

"Remember," her mom said, getting back in the car. "You've got my video phone number if you need anything at all!" And she drove off.

With no other choice, Dawn headed towards the entrance of the building, where there was a lady at a desk. "Name?" she asked.

"Dawn Berlitz."

The woman smiled. "Welcome! Here's your dorm key," she said, handing Dawn a key with a tag that said: 876. She stuck it in her backpack.

"Thank you!"

She looked at her classes. "First I have Pokemon History with Professor Oak, apparently," Dawn said to no one. "In class...B8!" She looked around. The doors around her said: D4, D5, D6...

"Need help finding your class?"

Dawn whirled around to see a boy with green hair. "Yes," she said, thankfully. "I'm Dawn, and I need to find classroom B8."

The boy smiled. "B8?" he said. "We're in the same class. I can escort you there with me. I'm Drew, by the way," he added, producing a rose so quickly, it seemed like it materialized out of thin air. He handed it to Dawn. "Pleasure to meet you."

"Hey, Drew, stop flirting with the new girl!" said a girl with ginger hair, walking up. "Make her feel comfortable! You're Dawn, right? I'm Misty! Nice to meet you!"

"Nice to meet you too," Dawn replied, smiling.

"Oh, look, we're here," said Drew, as they approached a door with B8 inscribed into it. "Hopefully we're not late."

They walked into the classroom. There was no teacher there, but as soon as Dawn entered the room, there was whispering.

"A new girl?"

"I wonder what her name is."

"I hope she's nice."

Dawn blushed especially when a blond boy leaned over to a boy with spiky brown hair, and whispered, "Look at her, she's a total knockout!"

Dawn awkwardly headed towards the back of the room, and sat down next to a boy with purple hair (manly). "Hey," she tried, but the boy ignored her. 'Well, then,' she huffed in her mind. 'How rude.'

An older man who Dawn guessed was the teacher walked in, suddenly. "Settle down, everybody, I'll do the roll call!" he said, and everybody settled down into their seats.

"Ash Ketchum!"

A kid with black hair and a Pikachu on his shoulder stood up. Dawn found it strange that he brought a Pokemon to class, but nobody else seemed to find it abnormal.

"Gary Oak!"

The kid with the spiky brown hair stood up. Dawn immediately noticed that quite a few pairs of female eyes were on him. He must be the dreamy, fangirl-collecting boy, she decided.

"Barry Andersen!"

The blond kid stood up. Dawn could tell that he was the goofball of the class. He had that manic glint in his eye, and everybody was grinning at him.

Drew and Misty were also called.

"Dawn Berlitz! Our new student!"

Dawn stood up while everybody looked at Dawn. "Hi," she said, awkwardly, and sat down.

There was May, a friendly looking girl with light brown hair, Iris, a tan girl with a large amount of dark purple hair, Zoey, a cool looking redhead, and Trip, a quiet, yet sarcastic boy with light brown hair.

"Paul Jacobsen!"

The quiet boy next to Dawn stood up.

So, she knew all their names...She wondered what impact they would have on her life.

 **Sorry that was kinda short. I hope you are enjoying the story so far!**


	2. Chapter 2: Paul is officially a jerk

Dawn rushed to her next class.

"D7, D7..." she said, scanning the hallways. She suddenly slammed into someone. "Oh my gosh, I'm so sorry!" she cried, standing up.

"Why don't you watch where you're going?" It was Paul, from earlier. Dawn folded her arms.

"Excuse me! Next time I won't say sorry!" she fumed. He shrugged.

"Whatever, just stay out of my way," he said, walking away.

"Well!" Dawn huffed. "If he was any colder, he'd be an iceberg!"

"Oh, don't take it personally," someone behind her said. She turned around to see the girl named May from her class. "That's just how Paul treats everyone. You're Dawn, right? I'm May, great to meet you!"

Dawn smiled. "You too! You don't happen to know where classroom D7 is, do you?"

May nodded. "I'm in D7, too! It's this way!" And she led her to a classroom. They had assigned seats, so Dawn plopped down on the desk that had her number, 94. On her left was Misty, who smiled and waved at Dawn. On her right was Paul.

 _He's sitting next to me again?_ She thought. _Perfect._

A man in a labcoat with wavy black hair walked in. "Hello, students," he said, smiling at them all. "I am Professor Sycamore, you science teacher, and..."

He got echoey and far away as Dawn began to drift off. She came back, when she heard: "Dawn! Do you know the answer?"

"Uh..." she blushed. "I don't remember, what-"

A note suddenly hit her foot. She read it, and it said, **He asked you what it takes to evolve an Eevee into a Flareon.** She looked over at Paul, who tilted his head impatiently to the Professor.

"Uh, you use a Fire Stone!" she said quickly. He nodded.

"Good job, Dawn!" he said. "Now can anyone tell me how an Umbreon sheds it's tail?"

Later, after Science class, Dawn ran to catch up with Paul. "I just want to thank you for helping me out," she said.

"It'll be the first and the last time I help you with anything," he said coldly, and walked away.

 _What is with him?_ Dawn thought.


	3. Chapter 3: Girl Talk

**Hi! I'm hoping that this chapter will be a bit longer, but I'm not making any promises! So, read, and enjoy...**

Once school was finally over for the day, Dawn headed up to her dorm. She took out the key, and unlocked the door. Inside there was May, Misty, the ginger from earlier, and Iris, the girl who had a lot of thick, purple hair.

There were two bunk beds. One had Iris on the top and Misty on the bottom, the other had an empty top, and May on the bottom. Once May saw Dawn, she smiled and stood up. "Once I knew you were my roomate, I saved the top bunk for you," she said.

"Thanks," Dawn smiled.

"I say we take our new roomate out to the cafe to get some smoothies," Iris suggested. Everybody liked that idea, so they headed down to the cafe which was just down the street.

Once they got there, May ordereda Pecha smoothie, Iris ordered a Lum smoothie, Misty ordered a Pinap smoothie, and when it came to Dawn, she ordered the first thing she saw, a Leppa berry smoothie.

They settled down into a booth one they had ordered their food, and started to chat. "So, Dawn," Misty said, slyly. "Have any boys caught your eye, yet?"

Dawn blushed. "N-nobody yet," she muttered. "I haven't really been thinking about it..."

"But Paul hasn't made the best impression on her," May said, grinning. Iris looked up.

"Paul Jacobsen?" she asked. "I don't know much about him, except he's not a very popular person around here."

"Well, go figure!" Dawn exclaimed as their smoothies arrived. "He's a total jerk! And I sit next to him in each one of my classes! What kind of twist of fate is that?"

"Or maybe you like him," Misty said, in a teasing voice as she stirred her smoothie with a spoon. "And you pretend that you hate him so nobody will know."

"No way, jose!" Dawn said, disgusted. They all laughed.

"Okay, changing the subject," Misty chuckled. "Who do the rest of you guys like?" May blushed, and looked at the ground.

"Ash," she said in a small voice. Misty and Iris's mouths fell open.

"Ash? As in, Ash Ketchum?"

"He's a bit of a kid if you ask me."

"Yeah," May said, embarassed. "He's just so nice, and caring..."

"Okay, Iris," Misty said. "It's you. Who do you like?" Iris blushed.

"Nobody!" she said, obviously in denial. Misty studied her face, and gasped.

"It's Trip, isn't it?"

"What? NO!"

"Oh my gosh, it totally is!"

"Trip? No way, really?"

"Okay, I admit," Iris said, defeated. "I may like him just a tiny, tiny, tiny, tiny bit." May and Misty gasped.

"Oh, my gosh, I knew it!"

"Hey, Misty, who do you like?" Iris asked, defensively.

"Yeah, Misty, I've been meaning to ask you!" May exclaimed. Misty blushed deeper than the other two had.

"Um, well, it's a bit embarassing but, it's Tracey."

May gasped. Iris's jaw dropped. "You mean, that shy kid who's always drawing?" May asked. Misty nodded.

"I think I saw him in Art class earlier," Dawn said, slowly, thinking. "Yeah! Is he the one with the longer black hair?" Misty nodded again.

"Wait," Iris interrupted. "I thought you liked Ash."

"I did, for a short time," Misty said. "But I got over him."

They chatted for another half-hour or so, when suddenly, some other people entered the cafe. It was Barry, the goofy blond, Gary, the dreamy spiky brown hair guy, and Drew, the boy who'd shown her around that morning.

They stopped dead in their tracks when they saw the girls. Dawn could practically see their brains working at finding witty lines to impress them.

But all they could come up with was, "Hey."

"Hey," the girls said. They left the cafe soon after the boy's arrival.

"Let's head back to the dorm," May said. "It's getting late." They all agreed, and started back towards the school.

That night, Dawn called her mom. She smiled as her mom's face appeared on the computer screen. "Hi dear!" she said. "Any boyfriends, yet?"

Dawn sighed. "No, mom, but I do have some friends. Their names are May, Misty, and Iris."

She and her mom chatted for a bit before she shut the computer off, and went to bed. This new school wasn't so bad after all, she thought to herself, as she drifted off to the sound of May's snores.

 **How was it? Good? Terrible? Eh, whatever. This chapter wasn't as long as I wanted it to be, but oh, well. See you later!**


	4. Chapter 4: A split second

**Hi! I hope you're enjoying the story so far! In the upcoming chapters, I will switch to other characters POVs sometimes, but Dawn will remain the main character. And for the people who are wondering when the Ikarishipping will come in...BE PATIENT, IT'S COMING. Just kidding. It will be coming soon.**

 **And replying to BlackRubyADV: I love Advanceshipping too! I'm said it doesn't have a ton of supporters... :( And I'm planning some moments between them coming up in the next few chapters...**

 **And by the way, Dylan is just an OC. Anyway, on to the story!**

The next few days, Dawn enjoyed her classes, except for the fact that Paul was as cold as usual, and no matter how many times she tried to reach out to him in some way, he stayed as distant as usual, and she eventually gave up.

She figured out a few things about her fellow classmates over the week. Such as how May and Ash were always super awkward around each other (Dawn suspected Ash liked May also), and Iris and Trip argued a lot (love-hate, she got it). Barry WAS the goofball of the class, as she'd suspected, and he and Gary were not often seen apart (heheh, Barry and Gary rhyme...'kay, I'll stop now...), and Gary had a huge fanbase of girls, but he seemed to hate being followed around by them.

Dawn hung out a lot with Misty, May, and Iris. She learned a lot about their personalities, and their strenghths and weaknesses. Misty was a tomboyish girl, and apparently,she hated bugs and Bug type Pokemon. She lived at a Pokemon Gym, which explained her love of Water types. She also owned a Togepi. May was sort of in between girly and tomboyish, but her favorite color was definetly red. Practically everything she owned except her Torchic was red. And Iris was training to become a Dragon Master, a person whose specialty was Dragon type Pokemon. She owned an Axew, who hid in her mass of hair most of the time. She also, for some reason, hated Ice type Pokemon, and the cold. Though they were strange, Dawn could never remember having better friends.

They defended Dawn when someone teased her, supported everything that she did, and helped her out with homework and everything.

One night, Dawn had had a terrible day, and she decided to go have a walk outside. The sun was setting, and it was getting dark, but she didn't care. She kicked a rock, but almost tripped. "Ugh, why is everything I do awkward?" she said aloud. She sighed, and continued walking.

"Hey, Dawn!"

Dawn whirled around to see Dylan, a boy in her class who was obnoxious and rude. "What do you want, Dylan?" she snapped.

"You sure goofed up today in Science, huh? 'An Eevee evolves into Sylveon with a Shiny Stone,'" he mimicked.

Dawn rolled her eyes. "I don't have time to deal with you right now, Dylan."

"I also heard that you have no father, is that true?" Dylan sneered. Dawn stopped cold. Her father...His name was never mentioned in her house. Since...the accident...Dawn struggled to fight down tears, when she suddenly had memories flood back to her...

"HEY!"

Dawn turned around to see, to her surprise Paul. He had a look of concealed rage on his face. He marched towards Dylan who, even though Paul was much smaller than him, began to look concerned.

"P-Paul!" he stammered. "What do y-you want? Paul glared at him.

"Nobody is rude to her but ME! Got it?" he said, angrily. Dylan looked terrified.

"G-got it!" he squeaked and scampered off.

"Did you just...defend me?" Dawn asked, in awe.

"Don't think anything of it. I just hate bullies," Paul said, coldly, and began to walk away.

"Oh, no you don't!" Dawn yelled after him. "Don't you DARE walk away from me again, Paul Jacobsen!" Surprisingly, Paul turned around.

"All the time, over and over again, I get the impression that you're a jerk, and a rude person," Dawn exclaimed. "But then you reach out to me, and I think there's a good side to you. Then, when I go to thank you, you're the same, cold Paul! Who are you really?"

Paul was silent.

"Oh, I'm fed up!" Dawn cried, throwing her arms in the air, and walking away. Paul walked away in the opposite direction. But what Dawn didn't know, is that for a split second, Paul looked back at Dawn. For a split second.

 **Okay, done! I enjoyed making this chapter, actually, though in reality it was probably terrible. Once again, I apologize for the short chapters, and once again, I promise they will get longer. The Ikarishipping is finally coming in! Bye!**


	5. Chapter 5: Operation Cupid Takes Action!

**Before we begin, I'd just like to thank you for all the positive reviews, I appreciate them so much! And to reply to a couple of reviewers...**

 **Jpr123: Thank you! I try to give them dialogue as best as I can.**

 **LaprasIzLife: Thanks! I can't wait to get Ash and May together ;)**

 **One note. I'm gonna begin switching POVs, but the writing style is still gonna be in 3rd person, just focused on that character. Did that make sense?**

 **Now, on to the story!**

"Let me just tell you Dawn," Misty said. "Boys who defend you against bullies typically have a crush on you."

Dawn shook her head. "After the way he acts around me, I think he hates me." They were sitting in their dormitory, discussing what had happened on Dawn's walk. Iris hung off the top bunk by her legs.

"But sometimes when a boy acts like he hates you, he really likes you," she commented. Misty smiled slyly at her.

"Like Triiiiiip?" she teased. Iris fell off the bed on her head.

"That is NOT what I meant!"

May lied on the bottom bunk with her arms behind her head. "Why are boys so complicated?" she complained.

Misty shook her head. "If we knew the answer to that question, we'd be millionares."

"You don't understand," Dawn interrupted. "It was almost...scary, he got so mad. Even if he DID like me (not saying that he does), he wouldn't get THAT angry. It didn't take long for him to chase off Dylan."

"I just remembered something!" Iris said, popping up. "Not to change the subject, but next week is Christmas vacation, and it's Friday! A whole week off of school!"

"That'll give us plenty of time to crack the mysteries of Paul," May said, drowsily. "Can we go to sleep now?"

They all agreed, and after Dawn had her nightly chat with her mother, they went to sleep.

*THE NEXT MORNING*

(Barry's POV)

"Wakey wakey, Snorlaxes!" Barry cried, yanking the curtains to the side, bathing the dorm in sunlight. His roomates, Gary, Ash, and Drew all groaned.

"What time is it?" Ash asked drowsily.

"Oh, come on!" Barry protested, checking his watch. "It's only 7:30!"

"The point of Saturday is so we can _sleep in_ ," Gary grumbled into his pillow.

"I was having such a great dream," Drew complained, but he was the first to get out of bed.

"I have great plans for today!" Barry exclaimed, who was already dressed. "I'll explain in the cafeteria, now get dressed, will ya?"

They all sleepily pulled their clothes on, and headed down to the cafeteria. Once they'd all picked up their breakfast they sat at a table, and, by that time, they were awake enough to listen to Barry.

"Today is the perfect day to launch Barry Operation #57!" Barry said, enthusiastically. They all groaned.

"Barry, your 'operations' always lead to disater or detention," Gary said, skeptically. Barry shook his head.

"Today's will be a good one, I promise! I call it..." he leaned in closer, to whisper, "Operation Cupid."

"Operation-OH," Ash said in realization.

"Oh yes, this is gonna be good," Gary said, chuckling evilly.

"Who are we pairing up?" Drew asked curiously.

"Oh, a couple people," Barry said, glad they appreciated one of his ideas for once. "First up, we're gonna pair up Tracey and Misty."

"Tracey likes Misty?" Ash asked, surprised.

"Uh, DUH, Ash," Gary said. "He was drawing her in that notebook of his the other day."

"We need a girl's help," Barry said, grinning. "So I got Iris. Hey Iris, you can come over!"

Iris walked over. "Okay Barry, what did you want me to-" Suddenly, she fell over. They all looked over to see Iris and Trip sprawled on the ground.

Iris got up and and glared at Trip. "What was that?" she snapped. Trip stood up, also, and brushed himself off.

"I dunno," he said, sarcastically. "Maybe my fork got snagged in that GIANT hair of yours?" Then he marched off without another word.

"Anywaaaaaay," Barry said, loudly, catching Iris's attention again. "We wanted to ask you something."

"Okay, shoot."

"Does Misty like Tracey?" Barry asked. Iris looked around, and leaned forward.

"Yes, she actually does. Why do you ask?"

"We're trying to get them together, and we need some help," Barry explained. "Will you help?"

"Heck yeah!" Iris said, excitedly. "I've always wanted to do this!"

So they planned it out. Iris would give Misty a note, telling her to meet her at the beach. Barry would send Tracey the same thing. Ash and Drew even offered to let their Pokemon spice things up a bit. Gary would fly above on his Pidgeot, overseeing everything. He would contact them with a walkie-talkie if anything went wrong. An overused strategy, but an effective one.

So that evening, as the sun set, Barry and Iris went to hide in some bushes near the shore so they could see how their plan worked. Gary, as instucted, flew up above on Pidgeot. Ash and Drew were nowhere to be seen, but they trusted them with their mission.

As expected, Misty and Tracey both walked onto the beach at the same time. "Hi," Misty said to Tracey, a bit of shyness hidden in her voice.

"Hello," he replied, also a hint of shyness in his voice. "I'm waiting here for a friend, Barry."

"Funny," Misty said, smiling. "I'm here meeting my friend Iris."

They were silent for a moment. "And his sketchbook falls out now," Barry said, as a strong gust of wind (aided by Pidgeot) blew Tracey's sketchbook out of his bag (he never went anywhere without it, apparently. It flipped through a picture of a Marill.

"Aww!" Misty said, picking the book up. "What a cute, and accurate drawing!" And, as planned, she began to flip through the sketchbook, much to Tracey's unease.

She looked through it, oohing and aahing at all the great pictures, until she stopped at a picture of a familiar ginger-haired girl.

"Is this...?"

"Ah!" Tracey said, blushing. "I'm sorry! It's really embarassing, and-"

"But it's beautiful," Misty said softly. "It's extremely detailed, and amazingly accurate!"

"W-well," Tracey said, taking a deep breath. "I drew that, because, I uh, I've kind of had a crush on you since I began coming to this school, and I never told you."

And, right on cue, Ash's Squirtle used Bubble to make bubbles float over the water, looking amazing in the setting sun (Pokemon Mystery Dungeon reference, anyone?). Drew's Roselia cast rose petals into the light wind Pidgeot was making.

"Well," Misty said, blushing. "I kind of feel the same way."

They stood there for a moment, and Barry whispered to Iris, "We should give them some privacy." They beckoned to the others, who quietly left the scene.

As soon as they were out of earshot, they all cheered. "You guys did a great job!" Barry said, happily. "We should do this more often!"

 **Yes! A long chapter! Cross that off my Fanfiction bucket list! How was it? Mushy? Too cliche? Misty and Tracey are an odd couple, but a cute one. I know it being Christmas already in the story makes NO sense, but hey, it's Christmas, so why not add it too my Fanfiction? Hope you enjoyed it!**


	6. Chapter 6: At the Movies

**Okay, I reread my last chapter, and it was so cliche and rushed that I facepalmed. I'm sorry about that, and I will work on making my future chapters better. :/**

"NO WAY!"

Dawn was sitting in the cafeteria with her friends, and all of them were reacting differently to Misty confessing to them that she and Tracey were now dating. May had immediately squealed, and crushed Misty in a tight hug, saying, "I'm so happy for you!"

Dawn kept asking questions about what happened, and Misty was patiently answering them. Iris, for some reason, was unsurprised, and smiling in a way that made Dawn curious to what she was thinking about.

She glanced over at another table, where Tracey was talking to Barry, excitedly. Barry had the same reactions as Iris on his face. Dawn wondered what they knew about this.

Suddenly, Drew walked past their table. "Hey, Dawn," he said, giving her a rose, and then walking away.

"What is it with him and roses?" Dawn wondered aloud. May shrugged.

"They're just kinda his thing." Misty looked over at a table, and grinned at Dawn.

"Looks like someone's jealous." Dawn followed her gaze to see Paul, sitting at a separate table with Trip, glaring at Drew as he walked away.

"Jealousy when other boys flirt with you equals love," Iris said, winking at Dawn. Dawn remained indifferent.

"The way he hates me isn't love-hate, guys, it's hate-hate," she said, calmly. "Besides, I've noticed he doesn't typically like Drew, anyway."

The other girls looked at each other. They were all thinking around the same thing. _Ugh, she's so naive! When will she realize he actually likes her!?_

"So, ladies," Dawn said, changing the subject. "Where should we go, today?"

"We could go see that new movie," Iris suggested. "Y'know, _The Good Deino_?" (Hehe, see what I did there?)

They all agreed, and went to the movies.

*MEANWHILE*

(Gary's POV)

"Oh, c'mon, Ash," Gary said, rolling his eyes. "It's not that hard. Just walk up to her and tell her you like her."

"Easy for you to say!" Ash complained, as they walked into the movie theater. "May's just so...perfect. I'm not." They bought some popcorn and headed to their theater.

Drew snorted. "You're kidding. You know you guys are like, the same person, just opposite genders, right? Just ask her out to a meal, she'd enjoy that. What movie are we watching, again?"

" _The Good Deino,_ " Barry said as they walked into the theater. They stopped dead when they saw the girls sitting in the middle of one of the rows. _May's on the end of them,_ Gary thought. _Perfect._

"Ash," he said, shoving him. "You're _so_ sitting next to May." Ash struggled, but Gary forced him into the seat next to May. _You'll thank me for this later,_ he thought.

"Hi, May," Ash said, awkwardly. May blushed. As Gary had suspected, she liked him back. To confirm his suspicions, all the girls were grinning at May in that way that says, _Look who you're sitting next to..._ Then the movie started, and he redirected his attention to the movie.

In the middle of the movie, Gary glanced over at May and Ash. Their arms were on the same armrest. Their hands were touching. They both obviously knew, but didn't seem to mind, so neither moved their hands.

 _That was easy,_ Gary thought.

 **Okay, so that was a shorter chapter (like all of them, but look at it this way: instead of a couple long chapters, we'll have a bunch of short ones), but I just wanted to do a bit of Advanceshipping. Dawn, you're so naive! Bye for now!**


	7. Chapter 7: The Plot

**Alright, let's get right to the story this time. The Ikarishipping is approaching slowly, but surely. Please be patient. Once again, I'd like to thank everyone for all their support! You guys rock. :)**

As they exited the theater, Dawn suddenly noticed May was missing. "Where's May?" The girls all looked around, until they saw May talking to Ash. Ash was scratching the back of his head, nervously. He looked like he was asking May something. May grinned, blushing, and replied something. They waved goodbye to each other and headed to their different friends.

"Guess who just asked me out?" May asked, excitedly, sprinting up to them. They all squealed like little girls, and hugged May.

"Where are you going?" Misty asked.

"Denny's."

"He's taking her to Denny's for their first date?" Dawn muttered to Iris. Iris grinned.

"He knows the one way to her heart: breakfast food," she whispered back, smiling.

"We're going tomorrow evening," May continued, happily.

"I'm glad you two are happy, and all," Iris said. "But me and Dawn aren't having a lot of luck with guys at the moment."

"Hey!" Dawn interjected. "I never said I liked anybody!" The girls looked at her skeptically.

"C'mon, Dawn," May said, smiling. "You secretly like someone, I can tell by the way you deny it."

Dawn blushed. "I swear! I don't!"

"You do," Misty said, simply. "But we won't inquire you any further than that." They headed back to their dorm.

(May's POV)

May couldn't believe it! Ash Ketchum had just asked her out! She was in a daze the whole walk back to the school. But when they got back to their dorm, Misty beckoned to her and Iris. "Can we talk for a second, please?"

So they headed into the hallway, while Dawn stared after them, curiously. Iris shut the door. "What do you want to talk about, Misty?" she asked.

"She likes Paul, I can tell," Misty said, right off the bat.

"Why would you think that?" May asked.

"She keeps dropping clues," Misty explained. "The first time she talked about Paul, she seemed a little far away, if you know what I mean. Then when she was telling us about how he defended her, she had a touch of admiration in her voice. And then, this morning when we told her Paul liked her because of his jealousy of Drew, she blushed, ever so slightly."

"But those are all so subtle," Iris said, incredulously. "It doesn't mean she likes him."

"Even so," May interrupted. "It's obvious _he_ likes _her._ Have you _seen_ the way he stares at her? He helps her out in classes, defends her, gets jealous when Drew flirts with her...even though he tries to mask it with his cold personality, he's not very good at hiding how he feels. Either Dawn's extremely oblivious, or she knows, she just doesn't want to admit it."

"They would make a cute couple, their personalities being so different," Iris said, thoughtfully. "They just need a little push to get them going."

"And that's where we can help," Gary said, walking around the corner with Ash, Drew, and Barry.

"Gary Oak!" Misty shrieked, and glared at him. "Have you guys been eavesdropping?"

"That's not important," he replied. "All we're saying is, we can help you get them together. We've suceeded in the past to get people together, and we're practically experts."

"Yeah, you can help," May said quickly, before Misty could reply.

"We'll need a few days before we can do it, to plan it all out," Barry said. "Here, tomorrow, at lunch, we'll all meet and start plotting it out."

They all agreed, and parted.

"What took you so long?" Dawn asked, as they came back in.

"Oh, nothing," May said. "We were talking about a surprise for you." _You won't be expecting this one,_ she thought.

 **Okay, I'm no longer going to apologize for the short chapters. :/ Hope you enjoyed this chapter!**


	8. Chapter 8: The Date

**I apologize that I've been lazy for the last couple chapters, I've been trying to think up a better plot line. LaprasIzLife also recommended that I put the boys on some sort of sports team, so I'm gonna use that. This chapter will be focused a TON on Advanceshipping. Don't worry, Ikarishipping is still the main pairing, I'm just having writer's block when it comes to what I'm gonna do next for them. Anyway...**

(Ash's POV)

Ash was the first to wake up the next morning, which was strange for him. When Barry (who's usually the early bird) woke up, he asked Ash in disbelief, "Everything alright?"

"Yeah," Ash said, distantly. "I'm just worried I'm gonna totally blow it on my date tonight. I'd never so much as held a girl's hand until yesterday! In fact, I didn't understand love until I was twelve!"

Barry was shocked that Ash, who was usually so laid back and happy, could be so stressed. "Um, I don't really know about this kind of thing," he said, awkwardly. "But you could ask Drew or Gary for advice. They're better with girls, so people say."

As if on cue, Drew snapped up. "Wazzat?" he muttered, sleepily.

"Ah, it's nothing, Drew," Barry said. "But you should look at your hair. You've got the worst bedhead ever this morning."

"What?" Drew said, suddenly wide awake. "My hair? Bedhead?" He zoomed out to the bathroom.

"Gary! Wake up!" Barry yelled, throwing a pillow at him.

"I was having a good dream..." he muttered. Ash snorted.

"What, about the girlfriend you're never gonna have?" he asked, laughing.

"Watch it, Ashy boy," Gary grumbled, sitting up. Ash glared at him.

"DO NOT CALL ME ASHY."

"Okay, boys," Barry interrupted, brightly. "We've got a full day ahead of us! At lunch, we need to meet Misty, May, and Iris to start plotting operation 'Get Dawn and Paul together, somehow', and we need to get Ash ready for his big date!"

"Oh yeah," came Drew's voice, sarcastically from the bathroom. "The romantic dinner at Denny's."

"Hey, I know the one way to her heart is breakfast food," Ash said, defensively. "We've been friends since second grade."

"It's ironic you're taking her to a breakfast place for dinner," Gary said, smirking.

"ANYWAYYYYYY..." Barry interjected before Ash could respond. "Have we got everything checked off for our morning ritual? Ash and Gary fighting. Check. Me spelling out the day for us. Check. Drew obsessing over his hair. Check. Gary putting obscene amounts of hair gel in his hair to keep it spiky. Check. 'Kay, we can go to breakfast now."

They headed down to the cafeteria, where the special was french toast.

"Aw, heck yeah!" Ash cheered, pumping his fist, and dashed to join May in line.

"How's it going, Ash?" she asked. They'd got a lot more comfortable around each other after he'd got the guts to ask her out.

Ash shrugged. "Pretty good. I'm excited for tonight."

"Me too," May said, gratefully. "The other girls keep teasing me about it, though."

"I know, right?" Ash agreed, as the cafeteria lady dished their french toast onto their trays. "Gary and Drew are giving me a hard time about it."

May shrugged. "Eh, they're just jealous they don't have anyone to go out with," she decided. They had both filled up their trays, by then.

"Well, I'll see you later," Ash said.

"See ya!" May said, smiling. And they both went to sit at their separate tables.

*WEIRD TIME TRANSITION TO LUNCHTIME*

Ash, Gary, Drew, Barry, Iris, May, and Misty were all gathered at a table.

"How are we gonna do this?"

"Well, we need him to confess his feelings, somehow."

"That's not gonna be easy. He's the most introverted person I've met.

"Or we could get Dawn to confess her feelings."

"If she has any."

"We haven't decided if she likes him or not, remember?"

They plotted it for a while, but agreed to discuss it later, as Ash and May were out of it.

"I'll see you tonight?" Ash asked May, hopefully, as they parted ways.

"Yup," she agreed.

*YET ANOTHER TIME TRANSITION TO LATER THAT NIGHT*

Ash walked up to May's dorm room, and knocked on the door. He heard some scuffling, and Dawn opened the door. "Hey Dawn," Ash greeted. "Is May here?" Dawn giggled, and he heard more giggling in the background.

"Yeah, I'll go get her," she said, smiling. Ash stood there, feeling awkward as he heard whispering and giggling again. May sprinted to the door. The brunette was wearing a long sleeved red blouse and a black skirt.

"I didn't want to look too formal," she apologized. "Since we're only going to Denny's."

"Nah, you look great," Ash said. And he really meant it. May blushed. "So, since I don't have my driver's license quite yet," Ash continued, as they exited the school building. "We're taking the bus."

"Ooh, romantic," May teased. Ash laughed.

"Yeah, just be glad we're not walking in the snow," he replied, chuckling.

"Where's Pikachu?" May asked. Ash always carried his Pikachu around with him, but this time, it was nowhere to be found.

"Oh, Barry, Gary and Drew are watching him," Ash explained.

"I hope that works out for them," May joked, and they both laughed. Ash was happy already. May was just so...easy to be around. They could be on a date, but still joking like twelve year old's, just like old times. They took the bus to a stop nearby Denny's, and entered it.

There was practically no one there, and the waitress at the front seemed relieved for some business. "Right this way," she said, and guided them to a table. They both sat down, and took a look at their menus.

Once the waitress swung by again, they ordered their meals. They began to chat about taking care of their Pokemon, and talked about how weird their friends were, and made fun of Gary happily. They ate their meals, and headed back to the school.

Ash walked May back up to her dorm. Before she entered, she turned to him. "Thanks, Ash, I had a ton of fun," She said, truthfully, and kissed him on the cheek quickly. She walked into her dorm, leaving Ash with his cheeks burning.

He headed back to his dorm, expecting an electrocuted Gary holding Pikachu, an excited Barry asking him how it went, and Drew making snooty comments about May kissing him.

He was greeted with just what he was expecting.

 **Whew! This one took a while to write, and I think it's the longest one I've done so far, but I'm happy with it. It was fun to write because Ash and May have such great chemistry. Thanks for your continued support!**


	9. Chapter 9: Suddenly Supportive

**'Kay, I think I've got the plot figured out, but I think I might make a sequel to this story. I apologize if Trip's OOC. Enjoy!**

(Paul's POV)

Paul and Trip sat alone at a table in the cafeteria, eating lunch. They were both silent, since they weren't the most vocal people ever.

Paul and Trip weren't exactly friends, but they both were acceptant of each other, and connected in a way. Plus, they shared a dorm, so being acquainted was inevitable.

Paul, lost in thought, knocked his fork on the floor. A certain blunette was walking by, and picked it up. "Paul," she said, stiffly, handing him the fork.

"Dawn," he replied, coldly. She walked away. Trip shook his head.

"Man, what is your guy's deal? She's trying to befriend you, yet you act like you hate her," he commented. "I feel like the 'hate' is used to disguise feelings, though." He looked at Paul.

"Kind of like you and Iris," Paul pointed out. Trip stiffened.

"I do not like Iris, nor does she like me," he snapped.

"Really?" Paul pressed. "Because you take photos of her."

"Why would you think that?" Trip asked, stiffly. Paul held up Trip's camera.

"Camera's don't lie."

"Hey!" Trip said angrily, snatching the camera out of Paul's hands. "I told you not to look through my camera!"

Paul shrugged. Everybody knew nobody messed with Trip's camera, but Paul wasn't afraid of Trip. He knew he wouldn't do anything to him.

"Besides, you never denied that you had feelings for Dawn," Trip said, defensively. "You just changed the subject."

"And I never confirmed the fact! She doesn't mean anything to me!"

"Uh-huh, and you defended her against bullies because she means nothing to you."

"I just hate Dylan!"

"You just admit how you feel!"

"Admit to what?"

"The question is: do you have feelings for Dawn?!"

"I DON'T KNOW!"

Everybody in the cafeteria looked in surprise at Paul. He calmed down. "I don't know," he said, quietly. "I'm not quite sure how I feel."

"Hey," Trip said, calmly. "Just letting you know that I'm behind you all the way."

Paul was surprised at this supportive thing his acquaintance just stated. Maybe they were...more than acquaintances? Friends, possibly? He didn't know. He was in a world of confusion at the moment.

 **I know that was incredibly short, but I just wanted to do a Paul chapter, however long it was. Thanks for all your support!**


	10. Chapter 10: Opening Up

**Okay, this is it...The plot will take action! I'm really happy that you guys have enjoyed this story! I'm hoping this will turn out well...Let's see!**

(May's POV)

May lay on her bed, recounting the events of her date to her friends. They were all giggling and laughing, like teenage girls do.

"Wow, May," Misty said. "Not bad, for a first date."

"We should probably get some lunch," Iris said, checking the clock. Dawn laughed.

"Do you always have food on the brain, Iris?" she asked in an amused voice. They all laughed, but decided to go to the cafeteria anyway.

When they settled down, and began to eat, May looked up, and saw the boys beckoning frantically to them. She nudged Iris and Misty, who looked up from their food and saw the boys.

"Be right back, Dawn," Misty said, and they got up from the table, and headed over to the boys.

"What is it?" Iris asked, slightly miffed that she didn't get to finish lunch.

"We've talked to Trip," Gary said." And he's all for getting Dawn and Paul together. We asked him some questions about Paul, and the one we found most interesting was Paul's favorite place to hang out."

"Where?" Misty asked.

"You know that bench, underneath that big tree, overlooking that pond?" Barry asked. They all nodded. "Apparently, that's one of his favorite places to be. Trip said that he goes there every day at 4:30. We figured if we could get Dawn to go there at around the same time..."

"Oh..." May said, understanding. "Gotcha. Leave it to us."

So later, at 4:20, when Dawn prepared for her daily walk, Misty carefully dropped the hint.

"Dawn, I hear there's this really pretty place under the giant maple tree. There's a bench, and it overlooks a pond, and you should go there on your walk."

To their relief, Dawn smiled. "That sounds like a great idea! I'll go there, for sure." And when Dawn headed out, the girls and boys quietly followed her, to see how it would work out.

(Dawn's POV)

Dawn searched around. _Giant maple, giant maple..._ Aha! She spotted a large tree on a small hill. That must be it!

She rushed up the hill, and stood under the giant tree. It really was beautiful, she decided, as she looked at the pond. Suddenly, she heard an all too familiar voice.

"Oh. It's you."

Dawn looked over at a bench to her right she hadn't noticed until now. Sure enough, there sat Paul. She began to edge away, silently. She did NOT want to talk to him.

"Don't go away. I won't insult you, or anything."

She looked back over at him. Was he...asking her to stay? She sat on the bench next to him, with some hesitation. Surprisingly, he didn't move.

"It's pretty, isn't it?" Dawn asked, trying to make awkward conversation.

"Yeah."

Man, he was hard to converse with!

"Dawn?"

She looked at him, surprised. "You...said my name?"

"Yeah. What's so strange about it?"

"Well, most of the time, you call me something like, 'girl' or 'stupid' or 'you'."

"Hm, those do seem to be my nicknames for you," was the reply.

Dawn smiled, slightly. "What did you want to ask me?"

"I bet you were wondering why I defended you from Dylan."

"Well, yes, I was," Dawn said.

"Well, for one thing, Dylan's an idiot," he began. "Another, I understand what it's like to be teased about a dead or missing parent."

Dawn looked at the ground. "What...happened to my dad was that one day, we were driving. I was about five, and he was driving me home from my kindergarten class. Suddenly, a car in front of us swerved. It hit the car in front of it, and while my dad started to step on the brakes, we hit it, anyway. The car behind us also crashed into us. Our car was severely damaged. I made it out alive, but my dad...he..." She struggled not to cry. "That image is still traumatic in my mind, so whenever someone brings up my dad, I kind of break down."

"I'm sorry," Paul said, quietly. Dawn had never seen this side of Paul. He cared, he understood, he related...It was strange, yet comforting.

"I never knew my parents," he continued. "I was raised by my aunt Julia along with my older brother Reggie all my life. I was teased a lot in grade school about it. I became bitter. I feel like I'm still a bit bitter today."

They were both silent for a moment, staring at the Feebas swimming around in the pond.

Paul cleared his throat. "Another reason why I defended you is, well, ever since you arrived at this school, you've... intrigued me. Though I've never really cared about anyone except my aunt and my brother, something about you just...caught my attention." He blushed, lightly. Dawn was shocked. She'd never seen Paul this...well... _emotional_ before. She saw where he was going with this, and blushed, too.

"And I've been meaning to ask you something. Talking with you today was nice," he began, slowly, obviously thinking his sentence through. "And maybe we could do it again, sometime. If you want to."

"Paul," Dawn asked, smiling. "Are you asking me out?"

"Let's not put it that way," he said, looking away, the light, light pink returning to his cheeks. "Let's just put it, 'a boy and a girl, chatting together'. Okay?"

"I would really like that, Paul."

They exchanged phone numbers, so they could plan something later. As Dawn walked to her dorm, she thought about how Paul had opened up to her, and basically asked her out. She hoped she could see him again, soon. He seemed like an honestly nice person, once she'd got him to open up.

As she walked into the dorm room, where the girls were waiting for her, May asked, "You seem to have a lot on your mind, did something happen?" Dawn was silent for a minute, and took a deep breath before speaking.

"I have a lot to tell you."

 **Ta-da! I'm very proud of this chapter, and I'm so thankful for all your great reviews! I apologize if either characters were OOC in this chapter. Until next time**!


	11. Epilogue

**All right. The epilogue. I know this story was a little strangely abrupt, and unfinished, but I'm going to possibly make a sequel, and plan that out better. Thanks for all your reviews!**

(Dawn's POV)

It was summer. Dawn was on break, so she stayed home with her mother, and introducing her to all of her friends. She was currently laying on her couch, watching TV.

Her phone beeped. She looked at it. There was a message from Paul, whose contact had been named, "Grouchface" with affection.

 _Are we still on for tonight?_

Dawn sent a message back.

 _Yes. I've been meaning to ask you if you'd mind if Ash, May, Misty, Tracey, Iris, and Trip came along? It could be kind of a quadruple date!_

After a couple minutes, her phone beeped again. She looked down, expecting a no.

 _I suppose that's fine. It would be good to meet your friends, and I already know Trip, so it wouldn't be too bad._

Dawn smiled. Every other time she asked to introduce him to her friends, he'd declined, saying that they wouldn't like him. But today, he'd finally agreed.

 _Awesome! See you tonight!_ she typed.

"Mom," she called, as her mom walked past her. She turned around.

"Yes, dear?"

"I'm planning on heading out with Paul tonight. Would that be all right?"

Her mom smiled. "Together, alone?"

"N-no! We're going out with some friends!" Dawn denied, panicked.

Her mom kissed her on the forehead. "Of course, dear. You've grown up so much this last school year. I missed you."

Dawn hugged her mother. "I missed you too!"

"But be back before midnight," she added in her motherly voice.

Dawn laughed. "Of course, mom."

*LATER*

They all met at the mall. All of Dawn's friends cheerfully introduced themselves to Paul, who in turn introduced himself. She even thought she saw him smile. Or maybe it was a grimace. She couldn't tell.

He wasn't a bad guy, Dawn thought. He'd improved a lot since they began hanging out together, and she began to see his softer side.

Yes, she thought. She was beginning to be glad that they'd moved here.

 **It's over! Thank you SO much for all your reviews, you don't know how much they inspired me to keep writing this! Also, let me know if you want a sequel or not. Bye!**


	12. Chapter 12

I am going to start working on a sequel for this story, so staytuned and all that!


	13. SEQUEL INFO!

The sequel is up!


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